AM1 study of a β-carboline set: structural properties and potential reactivity

Abstract

A set of β-carbolines derived from norharman and its corresponding dehydro and tetrahydro derivatives has been studied by means of the semiempirical AM1 method. Geometrical parameters, protonation affinities and static reactivity indices have been examined. Structural properties and protonation sites are well described by calculations. Orientation of electrophilic attack on different centres is only partially predicted by the frontier indices. The role of the protonated molecules as reactive species is also discussed.